Top Remote Senior Level Sales Leadership Jobs in Boston, MA

Lead the North America services go-to-market as the sales-facing professional services leader. Drive services positioning and attach rates, manage escalations, ensure high-quality value delivery, oversee at‑risk renewals, and represent PS in QBRs. Coach and develop teams, partner with sales on complex deals, and translate systemic issues into actionable improvement plans tied to commercial outcomes.

Lead Runpod’s Americas sales organization and revenue number across new business, expansion, and renewals. Manage and coach Account Executives and Account Managers, oversee forecasting and pipeline, lead complex enterprise deals and contract negotiations, build regional go-to-market strategy and sales playbooks, and convert product-led demand into revenue. Partner with Marketing, Product, Legal, and Finance while improving sales efficiency through AI and developing a remote-first team.

Lead and build Toast Retail’s Mid-Market sales function from the ground up. Manage and coach Account Executives while personally closing complex grocery, liquor, and convenience retail deals. Develop repeatable sales processes, qualification frameworks, business cases, proposals, forecasting practices, and competitive positioning. Partner cross-functionally with Product, Marketing, Enablement, Finance, Deal Desk, and Onboarding to support enterprise implementations and product improvements. Hire and develop a high-performing team, establish benchmarks, and transition from a player-coach role to full team leadership.

Lead the US Higher Education sales team, coach sales excellence, build successful sales teams, and manage territory planning, assessment, and resource allocation. The role requires higher education leadership experience in software or SaaS, enterprise security familiarity, AI/ML understanding, and the ability to attract top sales talent and scale organizational processes.

Lead and scale a global team of Principal Agentic Technologists supporting strategic enterprise sales. Define technical sales methodologies, demonstrations, and proof-of-value frameworks for AI agent and non-human identity security products. Partner with sales, product, marketing, and engineering leaders to support major deals, influence product roadmaps, develop enablement programs, and communicate technical value to executives and architects.

Owns direct enterprise sales across a national territory of education employers, including universities, school districts, benefits pools, and associations. Manages prospecting, quotas, pipelines, and end-to-end RFP pursuits involving consultants, procurement, finalist presentations, and governance approvals. Builds strategic relationships with education benefits consultants, pool administrators, and benefits directors while communicating competitive value propositions. Requires deep health benefits and education-sector sales expertise, enterprise selling experience, data literacy, and sales process development skills.

Leads and develops a team of Account Managers, Account Executives, and Client Executives. Responsibilities include hiring, coaching, sales planning, territory assignment, customer and partner engagement, performance management, and achieving segment sales and profit goals. The role analyzes sales data, manages operating plans, supports customer outcomes, and drives team adoption of AI-enabled practices. Travel to customer meetings may reach 20%.

Leads Buick and GMC zone sales performance across dealership networks in Michigan. Builds dealer relationships, develops market-share and profitability strategies, coaches District Managers, oversees inventory, training, digital marketing, accessories, customer retention, facility compliance, and contractual performance. Drives business planning, sales growth, customer satisfaction, dealer engagement, and adoption of dealership tools. This field-based role requires frequent travel and residence in or relocation to the Detroit area.

Responsible for leading a sales team to develop and execute account strategies for Cloud Security, drive revenue growth, and manage relationships with major clients.

Lead and scale a team of Key & Enterprise Account Executives across US Travel, New Markets, and Canada. Drive GTM strategy, executive stakeholder management, complex deal negotiation, cross-functional deal orchestration, forecasting rigor, and post-close launch/expansion. Recruit, coach, and hold the team accountable while traveling regularly to accelerate deals and represent Affirm at industry events.